JP2010536892A - 4-Amidinobenzylamine for cosmetic and / or dermatological use - Google Patents
4-Amidinobenzylamine for cosmetic and / or dermatological use Download PDFInfo
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- JP2010536892A JP2010536892A JP2010522191A JP2010522191A JP2010536892A JP 2010536892 A JP2010536892 A JP 2010536892A JP 2010522191 A JP2010522191 A JP 2010522191A JP 2010522191 A JP2010522191 A JP 2010522191A JP 2010536892 A JP2010536892 A JP 2010536892A
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- Prior art keywords
- acid
- skin
- extract
- alkyl
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- 239000002537 cosmetic Substances 0.000 title claims abstract description 20
- CHOGNBXWAZDZBM-UHFFFAOYSA-N 4-(aminomethyl)benzenecarboximidamide Chemical compound NCC1=CC=C(C(N)=N)C=C1 CHOGNBXWAZDZBM-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 230000004888 barrier function Effects 0.000 claims abstract description 13
- 206010013786 Dry skin Diseases 0.000 claims abstract description 10
- 230000037336 dry skin Effects 0.000 claims abstract description 10
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- 208000001840 Dandruff Diseases 0.000 claims abstract description 6
- 208000003251 Pruritus Diseases 0.000 claims abstract description 6
- 239000000499 gel Substances 0.000 claims abstract description 5
- 239000002453 shampoo Substances 0.000 claims abstract description 5
- 230000007803 itching Effects 0.000 claims abstract description 4
- 239000006210 lotion Substances 0.000 claims abstract description 4
- 230000008447 perception Effects 0.000 claims abstract description 4
- 230000037307 sensitive skin Effects 0.000 claims abstract description 4
- 239000008406 cosmetic ingredient Substances 0.000 claims abstract description 3
- 230000037365 barrier function of the epidermis Effects 0.000 claims abstract 2
- 108090000435 Urokinase-type plasminogen activator Proteins 0.000 claims description 36
- 210000003491 skin Anatomy 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 22
- -1 phytosterols Chemical class 0.000 claims description 21
- 239000004615 ingredient Substances 0.000 claims description 17
- 239000000284 extract Substances 0.000 claims description 16
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
本発明は、化粧成分としての4−アミジノベンジルアミン誘導体の使用及び化粧用組成物並びに皮膚及び頭皮の化粧処置のための非治療的方法に関する。該誘導体及び組成物は、表皮バリアの損傷を予防および回復させるためのウロキナーゼ阻害剤として使用することができる。バリア異常及び破壊は、多くの場合に乾燥肌状態、痒み、フケ及び敏感肌の知覚の出発点である。これらの4−アミジノベンジルアミン誘導体は、クリーム、ローション、ゲル、シャンプーなどの形状で皮膚及び頭皮ケアの局所適用に使用することができる。 The present invention relates to the use of 4-amidinobenzylamine derivatives as cosmetic ingredients and cosmetic compositions and non-therapeutic methods for cosmetic treatment of the skin and scalp. The derivatives and compositions can be used as urokinase inhibitors to prevent and ameliorate epidermal barrier damage. Barrier anomalies and destruction are often the starting point for dry skin conditions, itching, dandruff and sensitive skin perception. These 4-amidinobenzylamine derivatives can be used for topical application in skin and scalp care in the form of creams, lotions, gels, shampoos and the like.
Description
発明の背景
ウロキナーゼ(uPA)は、ウロキナーゼ型プラスミノーゲン活性化因子とも呼ばれ、多ドメイン性セリンプロテアーゼ(EC3.4.21.31)である。uPAは、三つのドメイン、すなわち成長因子様ドメイン(aa4−43)、クリングルドメイン(aa47−135)及び触媒性「B」鎖(アミノ酸144−411)からなるアミノ酸残基411個のタンパク質である。クリングルドメインは、ヘパリンと結合すると思われる。成長因子様ドメインは、上皮成長因子(EGF)の構造と幾分類似性を有することから、EGF様ドメインと呼ばれる。uPAは、チモーゲン(プロuPA又は一本鎖uPA)として合成され、プラスミンによるLys158とIle159の間のタンパク質分解性切断により活性化する。結果として生じる2本の鎖は、ジスルフィド結合により一緒に保たれる1。
Background of the Invention Urokinase (uPA), also called urokinase-type plasminogen activator, is a multidomain serine protease (EC 3.4.21.31). uPA is a protein of 411 amino acid residues consisting of three domains, a growth factor-like domain (aa4-43), a kringle domain (aa47-135) and a catalytic “B” chain (amino acids 144-411). The kringle domain appears to bind heparin. Growth factor-like domains are called EGF-like domains because they have some similarity to the structure of epidermal growth factor (EGF). uPA is synthesized as a zymogen (pro-uPA or single-stranded uPA) and activated by proteolytic cleavage between Lys158 and Ile159 by plasmin. The resulting two chains are held together by disulfide bonds 1 .
uPAは、平滑筋細胞、線維芽細胞、内皮細胞、マクロファージ及び腫瘍細胞などの多様な種類の細胞により産生される。uPAは、細胞浸潤及び組織リモデリングに主な役割を果たすことに関連づけられた2。 uPA is produced by various types of cells such as smooth muscle cells, fibroblasts, endothelial cells, macrophages and tumor cells. uPA has been implicated in playing a major role in cell invasion and tissue remodeling 2 .
細胞外マトリックスにおいてuPAは、特異的細胞表面レセプターであるuPAレセプター(uPAR)とそれの相互作用により細胞膜に繋がれている。結合相互作用は、おそらくEGF様ドメインにより仲介されると思われる。活性uPAへのプロuPAの切断は、プロuPA及びプラスミノーゲンがレセプターに結合している場合に加速する。故に、セリンプロテアーゼであるプラスミンは、プロuPAを活性化し、それが今度はプラスミノーゲンを切断することによって、より多くのプラスミンを活性化する。血漿中には大過剰のプロテアーゼ阻害剤が見られることから、この正のフィードバックサイクルは、おそらく細胞表面でのレセプターに基づくタンパク質分解に限定されると思われる1。 In the extracellular matrix, uPA is linked to the cell membrane by its interaction with the specific cell surface receptor uPA receptor (uPAR). The binding interaction is probably mediated by the EGF-like domain. Cleavage of pro-uPA to active uPA accelerates when pro-uPA and plasminogen are bound to the receptor. Hence, the serine protease plasmin activates pro uPA, which in turn activates more plasmin by cleaving plasminogen. This positive feedback cycle is likely limited to receptor-based proteolysis at the cell surface, as a large excess of protease inhibitors is found in plasma 1 .
uPAの最も重要な内因性阻害剤は、セルピン類、すなわちプラスミノーゲン活性化因子阻害因子−1(PAI−1)及びプラスミノーゲン活性化因子阻害因子−2(PAI−2)であり、これらは、プロテアーゼ活性を非可逆的に阻害する。 The most important endogenous inhibitors of uPA are serpins, plasminogen activator inhibitor-1 (PAI-1) and plasminogen activator inhibitor-2 (PAI-2), these Irreversibly inhibits protease activity.
uPAに関する主な基質は、細胞表面に結合したuPAによりプラスミンに変換されるプラスミノーゲンである。uPAは、プラスミノーゲンの中の単一のペプチド結合に高度に特異的である。活性化したプラスミンは、細胞外マトリックス(フィブリン、フィブロネクチン、ラミニン、及びプロテオグリカン)の構成要素を分解し、マトリックスメタロプロテアーゼ(MMP)もまた活性化することで、コラーゲンの分解を促進する1、3、4。それらの活性は、細胞浸潤及び組織リモデリングを含む重要な過程を導き、それらの過程には、創傷治癒、骨リモデリング、血管形成、腫瘍浸潤性及び転移の拡大が含まれる2。 The main substrate for uPA is plasminogen which is converted to plasmin by uPA bound to the cell surface. uPA is highly specific for a single peptide bond in plasminogen. Activated plasmin degrades the components of the extracellular matrix (fibrin, fibronectin, laminin, and proteoglycan) and also activates matrix metalloproteases (MMPs) to promote collagen degradation 1,3, 4 . Their activity leads to important processes including cell invasion and tissue remodeling, which include wound healing, bone remodeling, angiogenesis, tumor invasiveness and metastatic spread 2 .
多種類の細胞が、プラスミン介在性タンパク質分解又は細胞外マトリックス(ECM)及び基底膜(BM)などの細胞外支持構造の改変の主開始因子としてuPAを使用する。細胞は、ECM及びBMにより提供される物理的フレームワーク内の組織および器官の中に存在し、移動し、互いに相互作用する。ECM内の又はBMを通過する細胞の移動は、局所タンパク質分解又はこれらの構造の改変を必要とし、細胞をそれらの細胞には従来利用できなかった隣接領域に浸潤させる5。 Many types of cells use uPA as the primary initiator of plasmin-mediated proteolysis or modification of extracellular support structures such as extracellular matrix (ECM) and basement membrane (BM). Cells reside in tissues and organs within the physical framework provided by ECM and BM, migrate, and interact with each other. Migration of cells within or across the ECM requires local proteolysis or modification of these structures, causing cells to invade adjacent areas previously unavailable to those cells 5 .
したがって、uPA阻害剤は、血管形成、関節炎、炎症、浸潤、転移、骨粗鬆症に対して活性を有し、腫瘍の成長を阻害する3。 Therefore, uPA inhibitors have activity against angiogenesis, arthritis, inflammation, invasion, metastasis, osteoporosis and inhibit tumor growth 3 .
uPAが広範囲の浸潤性生物学的過程を仲介することから、強力で選択的なuPA阻害剤の有用性に注目が集まっている2。 Because uPA mediates a wide range of invasive biological processes, attention is focused on the usefulness of potent and selective uPA inhibitors 2 .
第VII因子、第X因子及び組織型プラスミノーゲン活性化因子(tPA)などのトリプシン様特異性を有するセリンプロテアーゼが多数存在するために、強力で選択的なuPA阻害剤の開発は難問である。構造に基づく大規模な薬物開発は、uPAの強力で選択的な阻害剤を提供した。これらは、一般に芳香族又は複素環骨格に構築されたアミジン又はグアニジン官能基を有するアルギニノ模倣体である6。 The development of potent and selective uPA inhibitors is challenging due to the presence of many serine proteases with trypsin-like specificity such as Factor VII, Factor X and tissue-type plasminogen activator (tPA) . Large-scale structure-based drug development has provided potent and selective inhibitors of uPA. These are arginino mimetics with amidine or guanidine functional groups that are generally built on aromatic or heterocyclic skeletons 6 .
異なる身体部位、異なる季節及び角質層の異なる空間的レベルでのSCの構造、組成及び機能における変化は、過去数十年にわたり化粧品業界にとって高まり続ける関心の的であった。例えば、角質層の脂質又はNMF(天然保湿因子)のレベルの差は、異なる身体部位に生じることが知られており、冬季数ヶ月のレベル低下及びそれらのレベル減少は、角質層外層に向けて起こる。 Changes in the structure, composition and function of SC at different body parts, different seasons and at different spatial levels of the stratum corneum have been a growing concern for the cosmetic industry over the past decades. For example, differences in stratum corneum lipids or NMF (natural moisturizing factor) levels are known to occur in different body parts, with several months in winter and lower levels that are directed towards the outer stratum corneum Occur.
プロテアーゼ活性及び質量レベルの差もまた報告された。表皮は、皮膚における複数の活性、すなわち表皮の増殖、分化、脂質バリアの恒常性及び組織リモデリングに関与する幾つかのセリンプロテアーゼを発現することが示された。最も重要なことに、他の酵素と共にセリンプロテアーゼによる角質層コルネオデスモソームのタンパク質分解は、落屑前の重大な事象である7。セリンプロテアーゼの過剰活性は、脂質プロセシング酵素の分解によるバリア撹乱を導くおそれがあり、それから高pHレベルでコルネオデスモソーム分解がコントロールされずに継続することに加えて、角質層の完全性及び合着もまた悪化させる8。 Differences in protease activity and mass levels were also reported. The epidermis has been shown to express several serine proteases involved in multiple activities in the skin, namely epidermal proliferation, differentiation, lipid barrier homeostasis and tissue remodeling. Most importantly, proteolysis of the stratum corneum corneodesmosome by serine proteases along with other enzymes is a critical event before desquamation 7 . Serine protease overactivity can lead to barrier perturbation due to degradation of lipid processing enzymes, and in addition to continued uncontrolled degradation of corneodesmosomes at high pH levels, stratum corneum integrity and coalescence also occur. It also worsens 8 .
角質層におけるセリンプロテアーゼは、基礎となる、時に観察できない皮膚炎のための主なマーカーでありうる。これに関して、プロテアーゼ阻害剤がバリア回復を支援することから、プラスミノーゲン/プラスミン系の活性上昇は、バリア回復を損なうと考えられる9。uPAは、バリア損傷後に活性化することが報告された10。uPA活性増加が、乾燥肌を有する被験者の頬からのテープストリッピングで観察され、これは、経皮水分喪失レベル増加と相関した11。プロテアーゼ阻害剤は、特に乾燥肌を軽減することが報告された9、10、11。 Serine proteases in the stratum corneum can be the main marker for underlying, sometimes unobservable dermatitis. In this regard, increased activity of the plasminogen / plasmin system appears to impair barrier recovery, as protease inhibitors assist in barrier recovery 9 . uPA has been reported to be activated after barrier injury 10 . Increased uPA activity was observed with tape stripping from the cheeks of subjects with dry skin, which correlated with increased levels of transdermal water loss 11 . Protease inhibitors have been reported to reduce dry skin, especially 9,10,11 .
Kitamuraら12は、さらに、正常な被験者の基底層だけに局在したプラスミノーゲンが、乾燥肌では全ての表皮細胞層に発現していたことを実証した。しかし、Kawaiら11は、uPAが角質層に存在し、この酵素が角質層におけるプラスミノーゲン系活性化のトリガーであったことを報告した。これは、個体の背中の皮膚に実験的に誘導された乾燥肌で上昇した。彼らは、さらに、uPA活性増加が視覚的乾燥肌を有する被験者及びTEWLレベルが上昇した被験者の頬からの角質層試料に存在したことを実証した。被験者が正常な外見の皮膚及び約16g m-2h-1未満のTEWLを有する場合、活性は見出されなかった。これらの結果は、バリア形成の異常又はバリア回復不全がTEWL及びプラスミン活性の上昇の結果として起こること、並びにバリア修復のための手段がプロテアーゼ阻害剤を使用することであろうということを示している。この事実に関わらず、被験者は、臨床的に正常に見える皮膚を有し、顔でのレベル上昇は、環境の影響によって誘導される、顔での準臨床的微小炎症状態が原因であるおそれがある。 Kitamura et al. 12 further demonstrated that plasminogen localized only in the basal layer of normal subjects was expressed in all epidermal cell layers in dry skin. However, Kawai et al. 11 reported that uPA was present in the stratum corneum and that this enzyme was a trigger for plasminogen activation in the stratum corneum. This was elevated with dry skin that was experimentally induced in the skin of the individual's back. They further demonstrated that increased uPA activity was present in stratum corneum samples from the cheeks of subjects with visually dry skin and subjects with elevated TEWL levels. No activity was found when the subject had normal-looking skin and TEWL of less than about 16 g m −2 h −1 . These results indicate that abnormalities in barrier formation or failure of barrier recovery occur as a result of increased TEWL and plasmin activity, and that the means for barrier repair will be to use protease inhibitors. . Despite this fact, subjects have skin that appears to be clinically normal, and increased levels on the face may be due to a subclinical microinflammatory condition on the face induced by environmental effects. is there.
バリア破壊の繰り返しは、表皮過形成を誘導し、乾燥肌を導くと考えられる10。 Repeated barrier disruption is thought to induce epidermal hyperplasia and lead to dry skin 10 .
驚くべきことに、国際公開公報第01/96286号4に記載されたuPA阻害剤が、乾燥性皮膚状態、痒み、フケ及び敏感肌の知覚などの皮膚及び頭皮バリア異常の局所処置に使用できることが見い出された。 Surprisingly, the uPA inhibitors described in WO 01/96286 4 can be used for topical treatment of skin and scalp barrier abnormalities such as dry skin conditions, itching, dandruff and sensitive skin perception. I was found.
発明の説明
本発明は、化粧成分としての、そして化粧用及び皮膚科学的組成物の製造のための、並びに皮膚の非治療的化粧処置法における4−アミジノベンジルアミン誘導体の使用に関する。該4−アミジノベンジルアミン誘導体は、一般式(I)で示される誘導体である
DESCRIPTION OF THE INVENTION The present invention relates to the use of 4-amidinobenzylamine derivatives as cosmetic ingredients and for the production of cosmetic and dermatological compositions and in non-therapeutic cosmetic treatment of the skin. The 4-amidinobenzylamine derivative is a derivative represented by the general formula (I)
[式中、
R1は、H、C1−C8−アルキル、場合により置換されたアリール−C1−C4−アルキル、アミノ−C1−C5−アルキル又はヒドロキシ−C1−C5−アルキルを表し;
R2は、H又はC1−C8−アルキルを表し;
R3は、ヒドロキシ−C1−C5−アルキル又はC1−C8−アルキルを表し;
R4は、H、−SO2−R、−CO−R、又は−COO−Rを表し;
R5は、H、OH、−CO−R又は−COO−Rを表し;
Rは、C1−C16−アルキル、場合により置換されたアリール、場合により置換されたヘテロアリール、場合により置換されたアリール−C1−C4−アルキル又は場合により置換されたヘテロアリール−C1−C4−アルキルを表し、そして
Xは、CH又はNを表す]。
[Where:
R 1 represents H, C 1 -C 8 -alkyl, optionally substituted aryl-C 1 -C 4 -alkyl, amino-C 1 -C 5 -alkyl or hydroxy-C 1 -C 5 -alkyl. ;
R 2 represents H or C 1 -C 8 -alkyl;
R 3 represents hydroxy-C 1 -C 5 -alkyl or C 1 -C 8 -alkyl;
R 4 represents H, —SO 2 —R, —CO—R, or —COO—R;
R 5 represents H, OH, —CO—R or —COO—R;
R is C 1 -C 16 -alkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted aryl-C 1 -C 4 -alkyl or optionally substituted heteroaryl-C Represents 1 -C 4 -alkyl and X represents CH or N].
好ましいのは、アミジノ官能基がフェニル環の4位にあり、かつ/又は
R1が、H、C1−C8−アルキル、場合により置換されたアリール−C1−C4−アルキル又はアミノ−C1−C5−アルキルを表し;
R2が、Hを表し;
R3が、ヒドロキシ−C1−C5−アルキルを表し;
R4が、−SO2−Rを表し;
R5が、Hを表し;
Rが、場合により置換されたアリール−C1−C4−アルキルを表し、そして
Xが、CHを表す、
一般式(I)で示される化合物である。
Preference is given to an amidino functional group in the 4-position of the phenyl ring and / or R 1 is H, C 1 -C 8 -alkyl, optionally substituted aryl-C 1 -C 4 -alkyl or amino- Represents C 1 -C 5 -alkyl;
R 2 represents H;
R 3 represents hydroxy-C 1 -C 5 -alkyl;
R 4 represents —SO 2 —R;
R 5 represents H;
R represents optionally substituted aryl-C 1 -C 4 -alkyl and X represents CH;
It is a compound shown by general formula (I).
さらに好ましいアミジノベンジルアミン誘導体は、ベンジルスルホニル−D−Ser−ホモPhe−(4−アミジノ−ベンジルアミド)、ベンジルスルホニル−D−Ser−Lys−(4−アミジノ−ベンジルアミド)、ベンジルスルホニル−D−Ser−Gly−4−アミジノ−ベンジルアミド及びベンジルスルホニル−D−Ser−Ala−4−アミジノ−ベンジルアミドである。これらの化合物は全て、強力で高度に特異的なウロキナーゼ阻害活性を示し、国際公開公報第01/96286号に記載されている4。これらの化合物は、純粋なエナンチオマーとして好都合に使用される。 Further preferred amidinobenzylamine derivatives are benzylsulfonyl-D-Ser-homo Phe- (4-amidino-benzylamide), benzylsulfonyl-D-Ser-Lys- (4-amidino-benzylamide), benzylsulfonyl-D- Ser-Gly-4-amidino-benzylamide and benzylsulfonyl-D-Ser-Ala-4-amidino-benzylamide. All of these compounds exhibit potent and highly specific urokinase inhibitory activity and are described in WO 01/96286 4 . These compounds are conveniently used as pure enantiomers.
「ヘテロアリール」という用語は、それ自体単独で、又はヘテロアリール含有基に関する構造要素として、一つ又は二つの環から構成される5〜11員芳香族系を表し、ここで、1〜3員は、酸素、硫黄及び窒素より選択されるヘテロ原子である。1〜2個のベンゼン環が縮合して複素環になってもよい。その例は、ピリジル、ピリミジニル、ピリダジニル、ピラジニル、1,3,5−トリアジニル、キノリニル、イソキノリニル、キノキサリニル、キナゾリニル、フタラジニル、ピロリル、ピラゾリニル、イミダゾリニル、1,2,4−トリアゾリニル、テトラゾリニル、フリル、チエニル、オキサゾリニル、チアゾリニル、イソチアゾリニル、ベンゾキサゾリル、ベンゾチエニル、インドリル、ベンズイミダゾリル、インダゾリル、ベンゾトリアゾリル及びベンゾチアゾリルである。結合は、ヘテロ部分又はベンゾ部分のいずれかで、そしてπ電子過剰ヘテロ芳香族化合物の窒素又は任意の炭素において生じうる。 The term “heteroaryl”, by itself or as a structural element for a heteroaryl-containing group, represents a 5- to 11-membered aromatic system composed of one or two rings, where Is a heteroatom selected from oxygen, sulfur and nitrogen. One or two benzene rings may be condensed to form a heterocyclic ring. Examples are pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,3,5-triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phthalazinyl, pyrrolyl, pyrazolinyl, imidazolinyl, 1,2,4-triazolinyl, tetrazolinyl, furyl, thienyl, Oxazolinyl, thiazolinyl, isothiazolinyl, benzoxazolyl, benzothienyl, indolyl, benzimidazolyl, indazolyl, benzotriazolyl and benzothiazolyl. The bond can occur either in the hetero moiety or the benzo moiety and at the nitrogen or any carbon of the π-electron rich heteroaromatic compound.
場合により置換されたアリール基及びヘテロアリール基の置換基は、例えば、ハロゲン、C1−C6−アルキル、C1−C6−ハロアルキル、ヒドロキシ、C1−C6−アルコキシ、C1−C6−ハロアルコキシ、C1−C6−アルケニル、C2−C6−アルケニルオキシ、C2−C6−アルキニル、C3−C6−アルキニルオキシ、C1−C6−アルコキシカルボニル、CN、OCN、ニトロ、アミノ、C1−C6−アルキルアミノ、ジ−C1−C6−アルキルアミノ、アミノカルボニル、C1−C6−アルキルアミノカルボニル、ジ−C1−C6−アルキルアミノカルボニル、C1−C6−アルキルチオ、C1−C6−アルキルスルホキシル、C1−C6−アルキルスルホニル及びC3−C6−シクロアルキルである。 The optionally substituted aryl and heteroaryl group substituents are, for example, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, hydroxy, C 1 -C 6 -alkoxy, C 1 -C 6 - haloalkoxy, C 1 -C 6 - alkenyl, C 2 -C 6 - alkenyloxy, C 2 -C 6 - alkynyl, C 3 -C 6 - alkynyloxy, C 1 -C 6 - alkoxycarbonyl, CN, OCN, nitro, amino, C 1 -C 6 - alkylamino, di -C 1 -C 6 - alkylamino, aminocarbonyl, C 1 -C 6 - alkylaminocarbonyl, di -C 1 -C 6 - alkylaminocarbonyl , C 1 -C 6 - alkylthio, C 1 -C 6 - alkylsulfoxyl, C 1 -C 6 - alkylsulfonyl and C 3 - 6 - cycloalkyl.
これらの化合物は、乾燥性皮膚状態、痒み、フケ及び/又は敏感肌の知覚のような皮膚及び/又は頭皮バリア異常の処置のためのクリーム、ローション、ゲル、シャンプーなどの形状で化粧品適用に使用することができる。 These compounds are used in cosmetic applications in the form of creams, lotions, gels, shampoos, etc. for the treatment of skin and / or scalp barrier abnormalities such as dry skin conditions, itching, dandruff and / or sensitive skin perception can do.
本発明の局所的に有効なベンジルアミン誘導体は、所望の任意の適用形状で利用可能に、又は調製することができる。故に、これらの製剤は、例えば水性又は無水調製物、油中水(w/o)若しくは水中油(o/w)型のエマルション若しくはマイクロエマルション、例えば水中油中水(w/o/w)型の多重エマルション、ゲル、シャンプー、固形剤、又はエアロゾルでありうる。本発明の製剤は、例えば粉末、湿式パッチ、ローション、クリーム若しくは軟膏、シャンプー及び洗浄製剤として、又は任意の他の化粧品として承認されている形状で利用することができる。ベンジルアミン誘導体の有効濃度は、化粧品の総重量に対して約0.001〜10000ppm、好ましくは0.1〜1000ppmである。 The topically effective benzylamine derivatives of the present invention can be made available or prepared in any desired application form. Thus, these formulations are for example aqueous or anhydrous preparations, water-in-oil (w / o) or oil-in-water (o / w) type emulsions or microemulsions, such as water-in-oil-in-water (w / o / w) type. Multiple emulsions, gels, shampoos, solids, or aerosols. The formulations of the present invention can be utilized, for example, as powders, wet patches, lotions, creams or ointments, shampoos and cleansing formulations, or in any other cosmetic approved form. The effective concentration of the benzylamine derivative is about 0.001 to 10000 ppm, preferably 0.1 to 1000 ppm, based on the total weight of the cosmetic.
製剤又は調製物にもすることができる本発明の化粧的に有効なベンジルアミン誘導体は、通常適用され局所適用可能な任意のさらなるスキンケア成分と一緒に使用することができる。追加的なスキンケア成分の例は、植物、藻類、微細藻類、酵母、キノコ、動物及び微生物、並びに以下のような合成及び半合成物質から得られる。
・メラトニン、尿素、クレアチニン、ジメチルエタノールアミン及びそれらの誘導体、
・アミノ酸及びそれらの誘導体(例えば、セリン、グリシン、アスパラギン、システイン、グルタミン、リシン、アルギニン、アスパラギン酸、グルタミン酸、N−アセチルシステイン、シトルリン)、
・タンパク質、それらの加水分解物及びそれらの誘導体(例えば、コラーゲン、ゼラチン、アルブミン、カゼイン、エラスチン、ケラチン、セリシン、フィブロイン、フィラグリン(fillagrin))、
・成長因子及びそれらの誘導体(例えば、形質転換成長因子、インスリン様成長因子、上皮成長因子、酸性及び塩基性線維芽細胞成長因子、神経成長因子、ケラチノサイト成長因子、肝細胞成長因子、血小板由来成長因子、顆粒球マクロファージコロニー刺激因子、血管内皮成長因子)、
・酵素及びプロテアーゼ並びにそれらの誘導体(パパイン、ブロメライン、スブチリシン、スーパーオキシドジスムターゼ、ラクトペルオキシダーゼ、ホスホリパーゼ、トランスグルタミナーゼ)、
・酵素阻害剤、プロテアーゼ阻害剤、及びそれらの誘導体(例えば、トラネキサム酸、ダイズトリプシン阻害剤、Bowman Birkインヒビター、LEKTI、アプロチニン、エラフィン、SLPI、α1−アンチトリプシン、α1−アンチキモトリプシン、コレステロール硫酸、ロイペプチン、キモスタチン、組織メタロプロテアーゼ阻害因子、Elhibin(登録商標)、Colhibin(登録商標)、Pefabloc(登録商標)シリーズの化合物、カラシエキス)、
・補酵素及びそれらの誘導体(例えば、ユビキノン、ニコチンアミド、ニコチンアミド アデニンジヌクレオチド、ニコチンアミド アデニンジヌクレオチドリン酸、コエンザイムA、コエンザイムB12、フラビンアデニンジヌクレオチド、フラビンモノヌクレオチド)、
・ジ−、トリ−、テトラ−、ペンタ−及びヘキサペプチドなどのペプチド並びにそれらの誘導体(例えば、カルノシン、H−βAla−Pro−Dab−NHベンジル、Cu(II)−H−Gly−His−Lys−OH、H−Gly−Leu−Phe−OH、エライジル−Lys−Phe−Lys−OH、パルミトイル−Lys−Val−Lys−OH、H−Lys−Pro−Val−OH、パルミトイル−Lys−Val−Dab−OH、H−Arg−Ser−Arg−Lys−OH、パルミトイル−Lys−Val−Dab−Thr−OH、H−Gly−Pro−Arg−Pro−Ala−NH2、パルミトイル−Lys−Thr−Thr−Lys−Ser−OH、アセチル−Glu−Glu−Met−Gln−Arg−ArgNH2)、
・単糖、二糖、三糖及びオリゴ糖などの糖質並びにそれらの誘導体(例えば、グルコース、フルクトース、マンノース、ジヒドロキシアセトン、エリトルロース、ショ糖、トレハロース、マルトース)、
・多糖及びそれらの誘導体(例えば、ガラクトマンナン、グルコマンナン、β−グルカン、カラゲナン、グリコーゲン、キトサン、レンチナン、リケニン、イヌリン、フコース、アルギネート、キシログルカン、デキストラン、アミロース、フルクタン、キサンタン、プルラン)、
・グリコサミノグリカン、それらのサブユニット並びにそれらの誘導体(例えば、ヒアルロナン、コンドロイチン硫酸、ヘパリン、デルマタン硫酸、グルクロン酸、N−アセチルグルコサミン)、
・プリン、ピリミジン、ヌクレオチド、ヌクレオシド及びそれらの誘導体(例えば、アラントイン、尿酸、アデノシン、アデノシン一リン酸、アデノシン5’−三リン酸、キネチン)、
・カルボン酸及びそれらの誘導体(例えば、乳酸、クエン酸、グリコール酸、アゼライン酸、サリチル酸、リポ酸、ピロリドンカルボン酸、ウロカニン酸、コーヒー酸)、
・脂肪酸及びそれらの誘導体(例えば、リノール酸、オレイン酸、パルミチン酸、共役リノール酸)、
・脂質及びそれらの誘導体(例えば、スクアラン、スクアレン、モノグリセリド、ジグリセリド、トリグリセリド、ワセリン、ラノリン)、
・スフィンゴシン、スフィンゴ脂質、スフィンゴ糖脂質、硫脂質及びそれらの誘導体(例えば、フィトスフィンゴシン、セラミド、グリコセラミド、セレブロシド、ガングリオブロシド、スルファチド)、
・リン脂質及びそれらの誘導体(ホスファチジルコリン、ホスファチジルセリン、ホスファチジルエタノールアミン)、
・ステロール、フィトステロール、サポニン及びそれらの誘導体(例えば、コレステロール、シトステロール、スチグマステロール、カンペステロール(kampesterol)、ルペオール、グリチルリジン)、
・フラボノイド及びそれらの誘導体(例えば、ルチン、ケルセチン、ゲニステイン、ダイゼイン、フィセチン、ミリセチン、ルテオリン、ヘスペレチン、シリビン、シリマリン、アピゲニン)、
・フェノール、ポリフェノール及びそれらの誘導体(例えば、エピガロカテキン、没食子酸エピガロカテキン、レスベラトロール、ノルジヒドログアヤレト酸、エラグ酸レゾルシノール)、
・テルペン及びそれらの誘導体(例えば、グリチルレチン酸、ファルネソール、α−ビサボロール、β−ビサボロール)、
・アルカロイド及びそれらの誘導体(例えば、カフェイン、テオフィリン、テオブロミン)、
・ベンゾフラン及びそれらの誘導体(例えば、ウスニン酸)、
・微量元素(例えば、Zn、Se、Mn)及びそれらの塩、
・ポリアルコール及びそれらの誘導体(例えば、グリセロール、プロピレングリコール、ブチレングリコール、ソルビトール、エリトリトール、ヘキサンジオール、フィタントリオール)、
・抗菌成分、抗菌ペプチド及びそれらの誘導体(例えば、ジンクピリチオン、デフェンシン、カテリシジン、ダームシジン、ヒスタチン)、
・UV吸収剤及びそれらの誘導体(例えば、ベンゾアート、アントラニラート、サリチラート、シンナマート、ベンゾフェノン(Parsol(商標)340など)、ベンズイミダゾール、ベンゾトリアゾール(Tinosorb(商標)Mなど)、トリアジン(Tinosorb(商標)Sなど)、ポリシリコーン(Parsol(商標)SLXなど)、酸化チタン、酸化亜鉛、メラニン、アヴォベンゾン)、
・ビタミン、プロビタミン及びそれらの誘導体(例えば、ビタミンA、一連のビタミンB類、ビタミンC、ビタミンD、ビタミンE)、
・レチノイド及びそれらの誘導体(例えば、レチノール、レチナール、トレチノイン、イソトレチノイン、アリトレチノイン、エトレチナート、アシトレチン、タザロテン、ベキサロテン)、
・カロテノイド及びそれらの誘導体(例えば、α−カロテン、β−カロテン、リコペン、ルテイン、ゼアキサンチン、アスタキサンチン)、
・キレート剤及びそれらの誘導体(例えば、EDTA、デスフェリオキサミン、フリルジオキシム)、
・保湿剤(例えば、グリセロール、ブチレングリコール、ソルビトール、尿素、N−アセチルグルコサミン、ヒアルロン酸、グリコサミノグリカン、アミノ酸、タンパク質加水分解物、コラーゲン、単糖、二糖、オリゴ糖及び多糖、Pentavitin(登録商標)、Phytaluronate(登録商標))、
・表皮バリア機能調節剤(例えば、セラミド、コレステロール、脂肪酸、スクアラン、フィトスフィンゴシン、ラノリン、レシチン、ワセリン)、
・皮膚改善(skin-revitalizing)成分及び再生成分(例えば、Revitalin(登録商標)-BT、酵母エキス、コンフリーエキス、イチョウエキス)、
・皮膚引き締め(skin tightening)及び抗シワ剤(例えば、ツボクサ、Vialox(登録商標)、Syn(登録商標)-Ake、Pefa(登録商標)-Tight、Matrixyl(登録商標)、Biopeptide CL、Kollaren PP、エライジル−Lys−Phe−Lys−OH、H−Arg−Ser−Arg−Lys−OH、アルジルリン、コラキシル、Dermican LS 9745)、
・緩和剤及び抗炎症剤(例えば、カモミールエキス、パンテノール、ナイアシンアミド、酸化亜鉛、アロエベラ、キンセンカエキス、甘草エキス、ハマメリス(hamamelis)エキス、Sensicalmine、アリスチン(Alistine)、H−Lys−Pro−Val−OH)、
・抗痒み成分(例えば、Stimu-Tex(登録商標)、月見草油)、
・抗フケ成分(例えば、アラントイン、硫化セレン、ビホナゾール、ジンクピリチオン)、
・落屑成分(例えば、α−ヒドロキシ酸、β−ヒドロキシ酸)、
・抗酸化剤(例えば、スーパーオキシドジスムターゼ、ユビキノン、リポ酸、ビタミンE、緑茶エキス)、
・皮脂調節及び/又は抗ニキビ剤(例えば、Regu(登録商標)-Seb、リノール酸、アフリカプルーンエキス、タイム(thymus officinalis)エキス、レゾルシノール、サリチル酸)、
・ストレッチマーク調節剤(例えば、ゴツコラエキス、ダルトシド、レジストリル(Registril))、
・皮膚免疫系調節剤(例えば、アルニカエキス、Immucell(登録商標))、
・皮膚ライトニング剤(例えば、α−アルブチン、β−アルブチン、コウジ酸、リン酸アスコルビルマグネシウム、甘草エキス、Melfade(登録商標)、メラノスタチン、アセチル−Asn−Ser−Leu−Asp−Phe−NH2)、
・皮膚タンニング剤(エリトルロース、ジヒドロキシアクテオン(dihydroxyacteone)、Melitane PP)、
・抗スリミング剤(例えば、カフェイン、テオフィリン、ガラナエキス、Regu(登録商標)-Fade)、
・皮膚微小循環調節剤(例えば、アルギニン、シリビン、シリマリン)、
・紅潮及び非一過性紅斑などの酒さの一次特徴を調節する薬剤(例えば、メトロニダゾール、アゼライン酸)、
・膿疹及び毛細血管拡張を調節する薬剤(例えば、シリマリン)、
・抗真菌成分(例えば、ケトコナゾール、シクロピロクス、チャノキ油)、及びそれらの混合物。
The cosmetically effective benzylamine derivatives of the present invention, which can also be a formulation or preparation, can be used with any additional skin care ingredients that are normally applied and topically applicable. Examples of additional skin care ingredients are derived from plants, algae, microalgae, yeast, mushrooms, animals and microorganisms, and synthetic and semi-synthetic materials such as:
Melatonin, urea, creatinine, dimethylethanolamine and their derivatives,
Amino acids and their derivatives (eg serine, glycine, asparagine, cysteine, glutamine, lysine, arginine, aspartic acid, glutamic acid, N-acetylcysteine, citrulline),
Proteins, their hydrolysates and their derivatives (eg collagen, gelatin, albumin, casein, elastin, keratin, sericin, fibroin, fillagrin),
Growth factors and their derivatives (eg transforming growth factor, insulin-like growth factor, epidermal growth factor, acidic and basic fibroblast growth factor, nerve growth factor, keratinocyte growth factor, hepatocyte growth factor, platelet derived growth Factor, granulocyte macrophage colony stimulating factor, vascular endothelial growth factor),
Enzymes and proteases and their derivatives (papain, bromelain, subtilisin, superoxide dismutase, lactoperoxidase, phospholipase, transglutaminase),
Enzyme inhibitors, protease inhibitors, and derivatives thereof (for example, tranexamic acid, soybean trypsin inhibitor, Bowman Birk inhibitor, LEKTI, aprotinin, elafin, SLPI, α1-antitrypsin, α1-antichymotrypsin, cholesterol sulfate, leupeptin , Chymostatin, tissue metalloprotease inhibitor, Elhibin®, Colhibin®, Pefabloc® series of compounds, mustard extract),
Coenzymes and their derivatives (eg ubiquinone, nicotinamide, nicotinamide adenine dinucleotide, nicotinamide adenine dinucleotide phosphate, coenzyme A, coenzyme B12, flavin adenine dinucleotide, flavin mononucleotide),
Peptides such as di-, tri-, tetra-, penta- and hexapeptides and their derivatives (eg carnosine, H-βAla-Pro-Dab-NH benzyl, Cu (II) -H-Gly-His-Lys) -OH, H-Gly-Leu-Phe-OH, Elidyl-Lys-Phe-Lys-OH, Palmitoyl-Lys-Val-Lys-OH, H-Lys-Pro-Val-OH, Palmitoyl-Lys-Val-Dab -OH, H-Arg-Ser-Arg-Lys-OH, Palmitoyl-Lys-Val-Dab-Thr-OH, H-Gly-Pro-Arg-Pro-Ala-NH2, Palmitoyl-Lys-Thr-Thr-Lys -Ser-OH, acetyl-Glu-Glu-Met-Gln-Arg-ArgNH 2 ),
-Carbohydrates such as monosaccharides, disaccharides, trisaccharides and oligosaccharides and derivatives thereof (for example, glucose, fructose, mannose, dihydroxyacetone, erythrulose, sucrose, trehalose, maltose),
Polysaccharides and derivatives thereof (eg galactomannan, glucomannan, β-glucan, carrageenan, glycogen, chitosan, lentinan, lichenin, inulin, fucose, alginate, xyloglucan, dextran, amylose, fructan, xanthan, pullulan)
Glycosaminoglycans, their subunits and their derivatives (eg hyaluronan, chondroitin sulfate, heparin, dermatan sulfate, glucuronic acid, N-acetylglucosamine),
Purines, pyrimidines, nucleotides, nucleosides and their derivatives (eg allantoin, uric acid, adenosine, adenosine monophosphate, adenosine 5′-triphosphate, kinetin),
Carboxylic acids and their derivatives (eg lactic acid, citric acid, glycolic acid, azelaic acid, salicylic acid, lipoic acid, pyrrolidone carboxylic acid, urocanic acid, caffeic acid),
Fatty acids and their derivatives (eg linoleic acid, oleic acid, palmitic acid, conjugated linoleic acid),
Lipids and their derivatives (eg, squalane, squalene, monoglycerides, diglycerides, triglycerides, petrolatum, lanolin),
Sphingosine, sphingolipids, glycosphingolipids, sulfated lipids and derivatives thereof (for example, phytosphingosine, ceramide, glycoceramide, cerebroside, gangliobroside, sulfatide),
Phospholipids and their derivatives (phosphatidylcholine, phosphatidylserine, phosphatidylethanolamine),
Sterols, phytosterols, saponins and their derivatives (eg cholesterol, sitosterol, stigmasterol, campesterol, lupeol, glycyrrhizin),
Flavonoids and their derivatives (eg rutin, quercetin, genistein, daidzein, fisetin, myricetin, luteolin, hesperetin, silybin, silymarin, apigenin),
Phenols, polyphenols and their derivatives (eg, epigallocatechin, epigallocatechin gallate, resveratrol, nordihydroguaiaretic acid, resorcinol ellagic acid),
Terpenes and their derivatives (eg glycyrrhetinic acid, farnesol, α-bisabolol, β-bisabolol),
Alkaloids and their derivatives (eg caffeine, theophylline, theobromine),
Benzofurans and their derivatives (eg usnic acid),
Trace elements (eg Zn, Se, Mn) and their salts,
Polyalcohols and their derivatives (eg glycerol, propylene glycol, butylene glycol, sorbitol, erythritol, hexanediol, phytanetriol),
Antibacterial ingredients, antibacterial peptides and their derivatives (eg, zinc pyrithione, defensin, cathelicidin, dermicidin, histatin),
UV absorbers and derivatives thereof (eg benzoate, anthranilate, salicylate, cinnamate, benzophenone (such as Parsol ™ 340), benzimidazole, benzotriazole (such as Tinosorb ™ M), triazine (Tinosorb ( Trademark) S), Polysilicone (Parsol (TM) SLX, etc.), Titanium oxide, Zinc oxide, Melanin, Avobenzone),
Vitamins, provitamins and their derivatives (eg vitamin A, a series of vitamins B, vitamin C, vitamin D, vitamin E),
Retinoids and their derivatives (eg retinol, retinal, tretinoin, isotretinoin, alitretinoin, etretinate, acitretin, tazarotene, bexarotene),
Carotenoids and derivatives thereof (for example, α-carotene, β-carotene, lycopene, lutein, zeaxanthin, astaxanthin),
Chelating agents and their derivatives (eg EDTA, desferrioxamine, furyldioxime),
-Moisturizers (eg glycerol, butylene glycol, sorbitol, urea, N-acetylglucosamine, hyaluronic acid, glycosaminoglycan, amino acids, protein hydrolysates, collagen, monosaccharides, disaccharides, oligosaccharides and polysaccharides, Pentavitin ( Registered trademark), Phytaluronate (registered trademark)),
・ Skin barrier function regulator (for example, ceramide, cholesterol, fatty acid, squalane, phytosphingosine, lanolin, lecithin, petrolatum),
-Skin-revitalizing and regenerating ingredients (eg, Revitalin (registered trademark) -BT, yeast extract, comfrey extract, ginkgo biloba extract),
-Skin tightening and anti-wrinkle agents (eg, Clover, Vialox (registered trademark), Syn (registered trademark) -Ake, Pefa (registered trademark) -Tight, Matrixyl (registered trademark), Biopeptide CL, Kollaren PP, Elidyl-Lys-Phe-Lys-OH, H-Arg-Ser-Arg-Lys-OH, Arzylline, Collaxyl, Dermican LS 9745),
-Relaxants and anti-inflammatory agents (eg chamomile extract, panthenol, niacinamide, zinc oxide, aloe vera, calendula extract, licorice extract, hamamelis extract, Sensicalmine, Alistine, H-Lys-Pro-Val -OH),
-Anti-itching ingredients (for example, Stimu-Tex (registered trademark), evening primrose oil),
・ Anti-dandruff ingredients (for example, allantoin, selenium sulfide, bifonazole, zinc pyrithione),
Desquamation components (for example, α-hydroxy acid, β-hydroxy acid),
・ Antioxidants (for example, superoxide dismutase, ubiquinone, lipoic acid, vitamin E, green tea extract),
-Sebum regulating and / or anti-acne agents (eg, Regu®-Seb, linoleic acid, African prune extract, thymus officinalis extract, resorcinol, salicylic acid),
-Stretch mark modifiers (eg, Gotsukola extract, daltside, Registril),
-Skin immune system regulator (for example, Arnica extract, Immucell (registered trademark)),
Skin lightening agent (for example, α-arbutin, β-arbutin, kojic acid, magnesium ascorbyl phosphate, licorice extract, Melfade (registered trademark), melanostatin, acetyl-Asn-Ser-Leu-Asp-Phe-NH 2 ) ,
・ Skin tanning agent (Erythrulose, dihydroxyacteone, Melitane PP),
Anti-slimming agents (eg caffeine, theophylline, guarana extract, Regu®-Fade),
・ Skin microcirculation regulator (eg, arginine, silybin, silymarin),
Drugs that modulate primary characteristics of rosacea such as flushing and non-transient erythema (eg, metronidazole, azelaic acid),
-Drugs that modulate impetigo and telangiectasia (eg silymarin),
-Antifungal ingredients (eg ketoconazole, ciclopirox, chanoki oil), and mixtures thereof.
許容され得る担体を、一般に本発明の化粧用活性組成物又は製剤の製造に使用してもよい。該担体の例は、アルコール、ポリオール、脂肪酸、脂質、油、ロウ、粘稠化剤、界面活性剤、乳化剤、充填剤、保存料、香料(aromas)及び芳香剤(fragrances)並びに着色剤、泡安定化剤及び/又はシリコーンである。 Acceptable carriers may generally be used in the manufacture of the cosmetically active composition or formulation of the present invention. Examples of such carriers are alcohols, polyols, fatty acids, lipids, oils, waxes, thickeners, surfactants, emulsifiers, fillers, preservatives, aromas and fragrances and colorants, foams Stabilizers and / or silicones.
本発明に使用されるべき担体は、特に、グリセリン、ポリグリセリン化合物、エチレングリコール、プロピレングリコール、ポリエチレングリコール、ポリプロピレングリコール、エチルアルコール、イソプロピルアルコール、寒天ガム、トラガカントガム、アラビアゴム、植物または動物性ゼラチン、メチルセルロース、エチルセルロース、カルボキシメチルセルロース、ヒドロキシメチルセルロース、ヒドロキシプロピルセルロース、アルギン酸ナトリウム、ポリビニルアルコール、ポリビニルアルコール酢酸エステル、セチルアルコールなどのC6−22脂肪アルコール、C6−22脂肪アルコールエステル、特に、ステアリン酸、パルミチン酸、ラウリン酸及び対応するメチル、エチル及びプロピルエステル、ラノリン、流動パラフィン又はワセリン若しくは蜜ロウなどの天然若しくは合成ロウ、オリーブ油、ヤシ油、ダイズ油、ヒマシ油などの植物油及び対応する硬化油、ポリアルキレンオキシドで修飾されたヒドロキシル含有化合物、並びに化粧品製剤に組み入れられることが公知のさらなる原料である。 Carriers to be used in the present invention are in particular glycerin, polyglycerin compounds, ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, ethyl alcohol, isopropyl alcohol, agar gum, tragacanth gum, gum arabic, vegetable or animal gelatin, C 6-22 fatty alcohols such as methyl cellulose, ethyl cellulose, carboxymethyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, sodium alginate, polyvinyl alcohol, polyvinyl alcohol acetate ester, cetyl alcohol, C 6-22 fatty alcohol ester, in particular stearic acid, palmitic acid Acids, lauric acid and the corresponding methyl, ethyl and propyl esters, lanolin, liquid para Incorporated into natural or synthetic waxes such as tin or petrolatum or beeswax, vegetable oils such as olive oil, coconut oil, soybean oil, castor oil and corresponding hardened oils, hydroxyl-containing compounds modified with polyalkylene oxides, and cosmetic formulations Is a further known raw material.
油中水(w/o)、水中油(o/w)又は水中油中水(w/o/w)エマルション又はマイクロエマルションの調製のために、本質的に公知であり、このために適用される化合物が好ましくは使用される。脂質相の調製のために、鉱物性又は天然の油又はロウが、好ましくは使用される。脂肪酸とエタノール、プロパノール、イソプロパノール、プロピレングリコール若しくはグリセリンとのエステル、又は脂肪アルコールと有機C3−20酸とのエステルなどの、脂肪酸とアルコールとの合成製造されたエステルもまた使用してもよい。例えば、ミリスチン酸プロピル、パルミチン酸イソプロピル、ステアリン酸イソプロピル、オレイン酸イソプロピル、ステアリン酸ブチル、ラウリン酸ヘキシル、ステアリン酸2−ヘキシルデシルなどの、ミリスチン酸、パルミチン酸、ステアリン酸、オレイン酸のエステル、若しくはホホバ油などの天然油、又はそれらの混合物が好ましい。好ましいシリコーンは、特に、好ましくは環状又は直鎖形状のポリシロキサンジメチルである。 Known per se for the preparation of water-in-oil (w / o), oil-in-water (o / w) or water-in-oil-in-water (w / o / w) emulsions or microemulsions and applied for this purpose. Are preferably used. For the preparation of the lipid phase, mineral or natural oils or waxes are preferably used. Synthetically produced esters of fatty acids and alcohols, such as esters of fatty acids with ethanol, propanol, isopropanol, propylene glycol or glycerin, or esters of fatty alcohols with organic C 3-20 acids may also be used. For example, myristic acid, palmitic acid, stearic acid, ester of oleic acid, such as propyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, butyl stearate, hexyl laurate, 2-hexyldecyl stearate, or Natural oils such as jojoba oil or mixtures thereof are preferred. A preferred silicone is polysiloxane dimethyl, particularly preferably in cyclic or linear form.
さらに、本発明の製剤は、好ましくは緩衝系として、pH調整のための酸又は塩基、例えば、水酸化ナトリウム、リン酸、クエン酸又は乳酸トリエタノールアミンを含みうる。 Furthermore, the formulations of the present invention may contain acids or bases for pH adjustment, such as sodium hydroxide, phosphoric acid, citric acid or lactate triethanolamine, preferably as a buffer system.
以下の実施例は、本発明の範囲をいかなる方法にも限定することなく、本発明をさらに具体的に説明することを意図する。 The following examples are intended to further illustrate the present invention without limiting the scope of the invention in any way.
実施例
実施例1
エマルションの調製
相Aの成分を70℃に、相Bの成分を75℃に加熱する。撹拌しながら相Bを相Aに注ぐ。その混合物を50℃に冷却し、均質化し、30℃に冷却する。次いで、相C及び相Dの成分を添加する。室温に達するまでこのエマルションを撹拌する。
Example
Example 1
Emulsion Preparation Heat Phase A ingredients to 70 ° C and Phase B ingredients to 75 ° C. Pour phase B into phase A with stirring. The mixture is cooled to 50 ° C., homogenized and cooled to 30 ° C. Phase C and phase D ingredients are then added. The emulsion is stirred until it reaches room temperature.
実施例2
化粧ゲルの調製
撹拌しながら相Aの成分を溶解させる。相BでpHを6.0に調整し、次いで相Cを添加する。
Example 2
Preparation of the cosmetic gel The ingredients of phase A are dissolved with stirring. Adjust the pH to 6.0 in phase B and then add phase C.
実施例3
角質層におけるTEWLとプラスミン及びuPA活性の相関
健康な白人被験者10人(皮膚タイプII−III)が試験に参加した。全ての志願者は、インフォームドコンセントの書式にサインした。頬に連続的なテープストリッピング(9回)(D-Squame(登録商標), CuDerm Corporation, Dallas, USA)を行う前に、Aquaflux AF103(Biox Systems, London, UK)を使用してTEWLを測定した。被験者に、角質層を採取する前の少なくとも12時間は、局所薬又は化粧料を全く適用しないよう要請した。最初に、テープストリッピング手順の15分前に、周囲温度の蒸留水を染みこませた綿パッドで皮膚を慎重に清浄し、乾燥させた。被験者を標準的な条件の環境室に順応させた。外科用マーカーで皮膚部位に印を付け、測定プローブ及びテープが同じ領域に一貫して確実に適用されるようにした。
Example 3
Correlation of TEWL with plasmin and uPA activity in the stratum corneum Ten healthy white subjects (skin type II-III) participated in the study. All applicants signed an informed consent form. TEWL was measured using Aquaflux AF103 (Biox Systems, London, UK) before performing continuous tape stripping (9 times) on the cheek (D-Squame®, CuDerm Corporation, Dallas, USA) . Subjects were asked not to apply any topical drugs or cosmetics for at least 12 hours before collecting the stratum corneum. First, 15 minutes prior to the tape stripping procedure, the skin was carefully cleaned and dried with a cotton pad soaked with ambient distilled water. Subjects were acclimatized to an environmental room with standard conditions. The skin site was marked with a surgical marker to ensure that the measurement probe and tape were applied consistently to the same area.
加圧装置(CuDerm Corporation, Dallas, USA)で225g/cm2の圧を5秒間かけて、直径2.2cm及び面積3.8cm2の標準D-Squame(登録商標)ディスクを皮膚に押しつけた。各ストリッピングの間隔は、20±5秒であった。 A standard D-Squame® disk having a diameter of 2.2 cm and an area of 3.8 cm 2 was pressed against the skin with a pressure device (CuDerm Corporation, Dallas, USA) at a pressure of 225 g / cm 2 for 5 seconds. The interval between each stripping was 20 ± 5 seconds.
赤外デンシトメーターSquameScan(商標)850A(Heiland electronic, Wetzlar、Germany)を用いた850nmでの吸光度測定により、テープストリッピングのタンパク質含量を定量した。SquameScan(商標)850Aは、標準D-Squame(登録商標)ディスクの適用のために特に設計されたものである。タンパク質定量のために、以下の式を使用した:
C(タンパク質)[μg cm-2]=1.366×吸光度[%]−1.557
The protein content of the tape stripping was quantified by absorbance measurement at 850 nm using an infrared densitometer SquameScan ™ 850A (Heiland electronic, Wetzlar, Germany). The SquameScan ™ 850A is specifically designed for standard D-Squame ™ disc applications. The following formula was used for protein quantification:
C (protein) [μg cm −2 ] = 1.366 × absorbance [%] − 1.557
吸光度の測定直後に、各テープストリッピングを1.5mlエッペンドルフチューブに移し、0.1Mトリス/HCl及び0.5% Triton X−100(pH8.0)から構成される750μlの緩衝液中で25℃及び1000rpmで15分抽出した。テープストリッピングの抽出液をプールした。その溶液250μlに蛍光ウロキナーゼ基質Bz−β−Ala−Gly−Arg−AMC(Pentapharm, Switzerland)及びプラスミン基質MeOSuc−Ala−Phe−Lys−AMC(Bachem, Switzerland)の5mMDMSO溶液1.25μlを添加した(最終基質濃度=25μM)。それらの溶液を37℃及び1000rpmで混合した。2時間後に、反応混合物100μlに100μlの1%酢酸を添加することにより反応を停止させた。放出されたAMCをC18 HPLC勾配溶出により定量した(80%水/20%アセトニトリル/0.07%TFAから50%水/50%アセトニトリル/0.07%TFA)。使用したカラムは、Symmetry C18、3.5μm、4.6mm×75mm(Waters, Milford, USA)であった。流速は1ml/min、インジェクション体積は5μl、AMCの保持時間は3.5分であった。発光波長は442nm、励起については354nmであった。 Immediately after measuring the absorbance, each tape stripping was transferred to a 1.5 ml Eppendorf tube and 25 ° C. in 750 μl buffer composed of 0.1 M Tris / HCl and 0.5% Triton X-100 (pH 8.0). And extracted at 1000 rpm for 15 minutes. Tape stripping extracts were pooled. To 250 μl of the solution was added 1.25 μl of a 5 mM DMSO solution of a fluorescent urokinase substrate Bz-β-Ala-Gly-Arg-AMC (Pentapharm, Switzerland) and a plasmin substrate MeOSuc-Ala-Phe-Lys-AMC (Bachem, Switzerland). Final substrate concentration = 25 μM). The solutions were mixed at 37 ° C. and 1000 rpm. After 2 hours, the reaction was stopped by adding 100 μl of 1% acetic acid to 100 μl of the reaction mixture. Released AMC was quantified by C18 HPLC gradient elution (80% water / 20% acetonitrile / 0.07% TFA to 50% water / 50% acetonitrile / 0.07% TFA). The column used was Symmetry C18, 3.5 μm, 4.6 mm × 75 mm (Waters, Milford, USA). The flow rate was 1 ml / min, the injection volume was 5 μl, and the AMC retention time was 3.5 minutes. The emission wavelength was 442 nm and the excitation was 354 nm.
表1及び図1にデータをまとめる。ヒト角質層最上層におけるuPA及びプラスミン活性の存在は、これらのプロテアーゼを局所適用された阻害剤により阻害することができると結論させる。 Table 1 and FIG. 1 summarize the data. The presence of uPA and plasmin activity in the human stratum corneum top layer concludes that these proteases can be inhibited by topically applied inhibitors.
図1:角質層におけるTEWLとプラスミン及びウロキナーゼ活性の相関。相関係数は、それぞれプラスミンに関してR2=0.95であり、uPAに関してR2=0.49であった。
Figure 1: Correlation of TEWL with plasmin and urokinase activity in the stratum corneum. The correlation coefficients were R 2 = 0.95 for plasmin and R 2 = 0.49 for uPA, respectively.
Claims (17)
[式中、
R1は、H、C1−C8−アルキル、場合により置換されたアリール−C1−C4−アルキル、アミノ−C1−C5−アルキル又はヒドロキシ−C1−C5−アルキルを表し;
R2は、H又はC1−C8−アルキルを表し;
R3は、ヒドロキシ−C1−C5−アルキル又はC1−C8−アルキルを表し;
R4は、H、−SO2−R、−CO−R,又は−COO−Rを表し;
R5は、H、OH、−CO−R又は−COO−Rを表し;
Rは、C1−C16−アルキル、場合により置換されたアリール、場合により置換されたヘテロアリール、場合により置換されたアリール−C1−C4−アルキル又は場合により置換されたヘテロアリール−C1−C4−アルキルを表し、そして
Xは、CH又はNを表す]
で示される少なくとも一つの化合物の使用。 The following general formula (I) as a cosmetic ingredient
[Where:
R 1 represents H, C 1 -C 8 -alkyl, optionally substituted aryl-C 1 -C 4 -alkyl, amino-C 1 -C 5 -alkyl or hydroxy-C 1 -C 5 -alkyl. ;
R 2 represents H or C 1 -C 8 -alkyl;
R 3 represents hydroxy-C 1 -C 5 -alkyl or C 1 -C 8 -alkyl;
R 4 represents H, —SO 2 —R, —CO—R, or —COO—R;
R 5 represents H, OH, —CO—R or —COO—R;
R is C 1 -C 16 -alkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted aryl-C 1 -C 4 -alkyl or optionally substituted heteroaryl-C Represents 1- C 4 -alkyl and X represents CH or N]
Use of at least one compound represented by
R2が、Hを表し;
R3が、ヒドロキシ−C1−C5−アルキルを表し;
R4が、−SO2−Rを表し;
R5が、Hを表し;
Rが、場合により置換されたアリール−C1−C4−アルキルを表し、そして
Xが、CHを表すことを特徴とする、請求項1及び2の一項記載の少なくとも一つの化合物の使用。 R 1 represents H, C 1 -C 8 -alkyl, optionally substituted aryl-C 1 -C 4 -alkyl or amino-C 1 -C 5 -alkyl;
R 2 represents H;
R 3 represents hydroxy-C 1 -C 5 -alkyl;
R 4 represents —SO 2 —R;
R 5 represents H;
R is optionally aryl -C 1 -C 4 substituted - alkyl, and X is characterized by representing a CH, use of at least one compound of one of claims 1 and 2.
a)ベンジルスルホニル−D−Ser−Gly−(4−アミジノ−ベンジルアミド)
b)ベンジルスルホニル−D−Ser−Ala−(4−アミジノ−ベンジルアミド)
c)ベンジルスルホニル−D−Ser−ホモPhe−(4−アミジノ−ベンジルアミド)
d)ベンジルスルホニル−D−Ser−Lys−(4−アミジノ−ベンジルアミド)
の少なくとも一つの使用。 Compound a) according to claim 1) benzylsulfonyl-D-Ser-Gly- (4-amidino-benzylamide)
b) Benzylsulfonyl-D-Ser-Ala- (4-amidino-benzylamide)
c) Benzylsulfonyl-D-Ser-homo Phe- (4-amidino-benzylamide)
d) Benzylsulfonyl-D-Ser-Lys- (4-amidino-benzylamide)
At least one use of.
b)アミノ酸、タンパク質、タンパク質加水分解物、成長因子、酵素、プロテアーゼ、酵素阻害剤、プロテアーゼ阻害剤、補酵素、ジ−、トリ−、テトラ−、ペンタ−及びヘキサペプチドなどのペプチド、単糖、二糖、三糖、オリゴ糖、及び多糖などの糖質、グリコサミノグリカン、グリコサミノグリカンサブユニット、プリン、ピリミジン、ヌクレオチド、ヌクレオシド、カルボン酸、飽和及び不飽和脂肪酸、脂質、スフィンゴシン、スフィンゴ脂質、スフィンゴ糖脂質、硫脂質、リン脂質、ステロール、フィトステロール、サポニン、フラボノイド、フェノール、ポリフェノール、テルペン、アルカロイド、ベンゾフラン、微量元素及びそれらの塩、ポリアルコール、抗菌成分、抗菌ペプチド、UV吸収剤、ビタミン、プロビタミン、レチノイド、カロテノイド、キレート剤、保湿剤、表皮バリア機能調節剤、皮膚改善(skin-revitalizing)及び再生成分、皮膚引き締め(skin tightening)及び抗シワ剤、緩和剤及び抗炎症剤、抗痒み成分、抗フケ成分、α−又はβ−ヒドロキシカルボン酸などの落屑成分、抗酸化剤、ラジカルスカベンジャー、UV消光剤、皮脂調節及び抗ニキビ剤、ストレッチマーク調節剤、皮膚免疫系調節剤、皮膚ライトニング剤、皮膚タンニング剤、抗スリミング剤、皮膚微小循環調節剤、紅潮及び非一過性紅斑などの酒さの一次特徴を調節する薬剤、膿疹及び毛細血管拡張を調節する薬剤、抗カビ剤、並びにそれらの混合物より選択される、少なくとも一つの追加的なスキンケア成分
を含有することを特徴とする化粧用組成物、特に局所適用可能な化粧用組成物。 a) at least one compound of general formula (I), and b) amino acids, proteins, protein hydrolysates, growth factors, enzymes, proteases, enzyme inhibitors, protease inhibitors, coenzymes, di-, tri- Peptides such as tetra-, penta- and hexapeptides, carbohydrates such as monosaccharides, disaccharides, trisaccharides, oligosaccharides and polysaccharides, glycosaminoglycans, glycosaminoglycan subunits, purines, pyrimidines, nucleotides, Nucleosides, carboxylic acids, saturated and unsaturated fatty acids, lipids, sphingosine, sphingolipids, glycosphingolipids, sulfated lipids, phospholipids, sterols, phytosterols, saponins, flavonoids, phenols, polyphenols, terpenes, alkaloids, benzofurans, trace elements and their Salt, polyalcohol, antibacterial composition , Antibacterial peptides, UV absorbers, vitamins, provitamins, retinoids, carotenoids, chelating agents, moisturizers, epidermal barrier function regulators, skin-revitalizing and regenerating ingredients, skin tightening and anti-wrinkle agents , Relaxation agents and anti-inflammatory agents, anti-itching ingredients, anti-dandruff ingredients, desquamating ingredients such as α- or β-hydroxycarboxylic acid, antioxidants, radical scavengers, UV quenchers, sebum control and anti-acne agents, stretch mark adjustment Agents, skin immune system regulators, skin lightening agents, skin tanning agents, anti-slimming agents, skin microcirculation regulators, drugs that regulate primary characteristics of rosacea such as flushing and non-transient erythema, abscesses and capillaries Contain at least one additional skin care ingredient selected from agents that modulate expansion, antifungal agents, and mixtures thereof. Cosmetic composition, characterized, in particular topically applicable cosmetic composition.
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Also Published As
Publication number | Publication date |
---|---|
EP2197409A1 (en) | 2010-06-23 |
CN101835449A (en) | 2010-09-15 |
WO2009026949A1 (en) | 2009-03-05 |
US20130224131A1 (en) | 2013-08-29 |
KR20100072000A (en) | 2010-06-29 |
US20110177140A1 (en) | 2011-07-21 |
KR101503958B1 (en) | 2015-03-18 |
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